Lakeville Vacation Rentals

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In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
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Oct 31 - Nov 2
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Nov 28 - Nov 30

Vacation Rentals in Lakeville

Our top choices for Lakeville vacation rentals

Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (47)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (28)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (9)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (30)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

Mid Century Modern Studio w/ Full Kitchen - Newly Built

9.6 out of 10, Exceptional, (4)
"We had a great stay, very cute town and close to our destination "
The price is ￥28,700
￥36,243 total
includes taxes & fees
Sep 7 - Sep 8
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is ￥52,852
￥100,300 total
includes taxes & fees
Sep 9 - Sep 10
Guesthouse Cabin vacation rentals in Berkshire County
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is ￥29,436
￥59,514 total
includes taxes & fees
Sep 4 - Sep 5
The Blue Elm - A Historic Berkshire Cottage
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Charming cottage with lake access, wood burning fire place, and WiFi
Smart TV, fireplace

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Dining

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is ￥59,384
￥105,629 total
includes taxes & fees
Sep 4 - Sep 5
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (23)
"We love being there do we extended our stay. Would have liked to stay even longer. Very relaxing and peaceful."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (19)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, table tennis, stereo

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (26)
"Overall it was a great location for a relaxing girls trip. The hot tub and sunroom were great places to hang out. The pictures were very accurate of the house. We did have some issues with cleanliness and pests that we were not expecting. We would recommend it for a relaxing lakefront thing stay."
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Lakefront Tranquility/Fishermans Delight
Interior

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (20)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lakeville Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Absolutely magical property. Ideal for Tanglewood, Great Barrington, and the Norman Rockwell Museum. We will definitely be back."
Janet 1-night trip
Posted 11 hours ago
Prospect Berkshires

Find out more about Lakeville

Find out more about Lakeville

Search for holiday rentals in Lakeville on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeville using one of the methods below:

  • View our selection of featured holiday rentals in Lakeville
  • Use the map to find apartments and other holiday homes in the Lakeville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeville while they last

Look no further and take a look at our great range of rental properties in Lakeville!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Lakeville?

Yes, we offer vacation rentals close to well known attractions in Lakeville, or you can select a secluded option if you'd like a relaxing place to stay. Lakeville is known for its restaurants and museums.

What are some of the best vacation home rentals that Lakeville has to offer?

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton: Located near Lakeville, this vacation home rental is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Lakeville?

Expedia has 14 vacation rentals for your stay in Lakeville.

What’s there to see and do in Lakeville?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Mount Frissell. Holley-Williams House Museum and Lime Rock Park are other places to visit while you're in town.

What’s a vacation rental in Lakeville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Lakeville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.